Thiourea → 4-(2,4,6-Trimethylphenyl)-1,3-thiazol-2-amine

HRID 2082403Notes

Reaction equation

HRID 2082403 reaction equation
BrC[CH2:3][C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])=O.[NH2:15][C:16]([NH2:18])=[S:17]>CO>[NH2:18][C:16]1[S:17][CH:3]=[C:4]([C:6]2[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=2[CH3:14])[N:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 536502472,4,6-Trimethylphenyl bromoethyl ketone

Product 1

HCID 6127164-(2,4,6-Trimethylphenyl)-1,3-thiazol-2-amineYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 80 g of 2,4,6-trimethylphenyl bromoethyl ketone and 35 g of thiourea in 250 ml of methanol is refluxed for 3 hours. After cooling the reaction mixture, the precipitate is filtered off and washed abundantly with diethyl ether. After concentration of the filtrate to a third of the initial volume, a second bath of crystals is recovered. Yield: 70%. m.p.=138° C. The hydrobromide prepared by the action of HBr in ethanol melts at 295° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe precipitate is filtered off
  3. washwashed abundantly with diethyl ether
  4. customAfter concentration of the filtrate to a third of the initial volume, a second bath of crystals is recovered
  5. customThe hydrobromide prepared by the action of HBr in ethanol melts at 295° C.

Sources & evidence

ORD record
ord-ec8910e8648944d5a6adc60f89f4182c
Source dataset
uspto-grants-1993_02
Patent number
US05189049

Reaction notes

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